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Synthesizing method for cephalosporin compound

A synthesis method and compound technology, applied in the direction of organic chemistry and the like, can solve problems such as unfavorable large-scale production, complex process operation, unfavorable environmental protection, etc., and achieve the effects of reducing production cost and environmental protection expenditure, saving solvent, and improving product yield.

Active Publication Date: 2012-03-14
QILU ANTIBIOTICS PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Crystallization, centrifugation, washing and drying are required in the process of synthesizing Formula 3, the process operation is complicated, and the use of a large amount of solvents in the centrifugation and washing steps is not conducive to environmental protection
In addition, there is also a low conversion rate in the process of silanization and dissolution of the compound of formula 3, which requires a new solvent, which is not conducive to large-scale production

Method used

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  • Synthesizing method for cephalosporin compound
  • Synthesizing method for cephalosporin compound
  • Synthesizing method for cephalosporin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] [Example 1] Preparation of formula 3 compound 7-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid intermediate

[0059] Get the acetonitrile complex of 600g boron trifluoride (wherein BF Content 17%, be converted into 1.504mol), 45g methylmercaptotetrazolium (0.388mol), 100g 7-aminocephalosporanic acid (0.366mol) put reaction bottle , reacted at 30°C for 1 h, and added 100 g of N,N-dimethylacetamide to obtain an intermediate solution of the compound of formula 3.

Embodiment 2

[0060] [Example 2] Preparation of formula 3 compound 7-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid intermediate

[0061] Get the dimethyl carbonate complex of 250g boron trifluoride (wherein BF3 content 40%, be converted into 1.475mol), 45g methylmercaptotetrazolium (0.388mol), 100g 7-aminocephalosporanic acid (0.366mol) , 400 g of dimethyl carbonate was placed in a reaction flask, reacted at 30°C for 1 h, and 100 g of N,N-dimethylformamide was added to obtain an intermediate solution of the compound of formula 3.

Embodiment 3

[0062] [Example 3] Preparation of formula 3 compound 7-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid intermediate

[0063] Put 45g of methylmercaptotetrazolium (0.388mol), 100g of 7-aminocephalosporanic acid (0.366mol), and 400g of diethyl ether into a reaction bottle, and feed 150g of boron trifluoride (gas) (2.214mol), and react at 30°C for 1h 100 g of triethylamine was added to obtain an intermediate solution of the compound of formula 3.

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Abstract

The invention relates to a synthesizing method for a cephalosporin compound. The method comprises the following steps of: making 7-aminocephalosporanic acid serving as a raw material react with methyl mercapto tetrazole in a solvent under the catalyzing action of boron trifluoride to synthesize a 7-amino-3-[(1-methyl-1H-tetrazole-5-radical)]-3-cephem-4-carboxylic acid intermediate, and adding an acid binding agent into a reactant solution for neutralizing to acid state; and directly preparing the obtained intermediate solution into cefoperazone acid, cefpiramide acid and cefamandole sodium without the purifying or drying the intermediate. The method has the advantages of simple process, small environmental pollution, high product yield, low cost and suitability for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of cephalosporin compounds, in particular to a synthesis process of cefoperazone acid, cefpiramic acid and cefamandole sodium. technical background [0002] Cephalosporins, also known as cephalosporins, are a class of broad-spectrum semi-synthetic antibiotics. The first cephalosporins came out in the 1960s, and currently there are more than 60 products on the market. Compared with penicillin, cephalosporin has the advantages of broad antibacterial spectrum, resistance to penicillinase, high curative effect, low toxicity, and less allergic reaction, etc., and occupies a very important position in anti-infection treatment. [0003] 7-Amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid is a synthetic cephalosporin cefoperazone, cefpiramide, An important intermediate of cefamandole sodium. The structure is as follows: [0004] [0005] The synthetic method of above formula 3 intermedi...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/06
Inventor 高阳汤沸王勇进董付敏孙永保李景昌
Owner QILU ANTIBIOTICS PHARMA
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